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Acta Cryst. (2011). E67, o1871    [ doi:10.1107/S1600536811024925 ]

Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

P. J. Seo, H. D. Choi, B. W. Son and U. Lee

Abstract top

In the title compound, C19H24O4S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by weak intermolecular C-H...O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.875 (4) and 0.125 (4).

Comment top

Recently, many compounds containing a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al. , 2009, Galal et al. , 2009, Khan et al. , 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al. , 2003). As a part of our ongoing study of the substituent effect on the solid state structures of ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues (Choi et al., 2007a,b; 2009), we report herein on the crystal structure of the title compound

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfinyl group (Table 1; C14—H14B···O4Ai), and the second one between an H atom of the benzylic methylene group and the O atom of the carbonyl group (Table 1; C15—H15B···O2ii).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2007a,b; 2009).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of ethyl 2-(5-cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (298 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 360–361 K; Rf = 0.41 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine, methylene, and 1.5Ueq(C) for methyl H atoms. The O atom of sulfinyl group is disordered over two positions with site-ccupancy factors, from refinement of 0.875 (4) (part A) and 0.125 (4) (part B). The S—O distances were restrained to 0.001 Å using command SADI and DELU.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B).
[Figure 2] Fig. 2. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x, y - 1, z; (ii) x, y + 1, z.]
Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate top
Crystal data top
C19H24O4SF(000) = 744
Mr = 348.45Dx = 1.325 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3275 reflections
a = 16.1065 (7) Åθ = 2.2–26.5°
b = 4.8485 (2) ŵ = 0.21 mm−1
c = 22.3653 (11) ÅT = 173 K
β = 91.010 (2)°Block, colourless
V = 1746.29 (14) Å30.28 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3804 independent reflections
Radiation source: rotating anode2917 reflections with I > 2σ(I)
graphite multilayerRint = 0.049
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.3°
φ and ω scansh = −20→19
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −6→6
Tmin = 0.945, Tmax = 0.964l = −28→28
15388 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: difference Fourier map
wR(F2) = 0.132H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0537P)2 + 1.3587P]
where P = (Fo2 + 2Fc2)/3
3804 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.56 e Å−3
67 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C19H24O4SV = 1746.29 (14) Å3
Mr = 348.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.1065 (7) ŵ = 0.21 mm−1
b = 4.8485 (2) ÅT = 173 K
c = 22.3653 (11) Å0.28 × 0.20 × 0.18 mm
β = 91.010 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3804 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2917 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.964Rint = 0.049
15388 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.132Δρmax = 0.56 e Å−3
S = 1.02Δρmin = −0.38 e Å−3
3804 reflectionsAbsolute structure: ?
229 parametersFlack parameter: ?
67 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.36614 (3)0.95799 (12)0.29116 (3)0.03096 (17)
O10.18470 (9)0.6531 (3)0.38601 (6)0.0325 (4)
O20.38323 (12)0.5969 (4)0.44371 (8)0.0532 (5)
O30.36351 (11)0.9044 (4)0.51602 (7)0.0443 (5)
O4A0.35467 (11)1.0448 (4)0.22886 (8)0.0392 (6)0.875 (4)
O4B0.3933 (9)1.160 (2)0.3361 (5)0.057 (4)0.125 (4)
C10.27598 (12)0.7963 (4)0.31809 (9)0.0266 (5)
C20.22021 (12)0.6069 (4)0.28840 (9)0.0253 (4)
C30.21169 (12)0.5003 (4)0.23082 (9)0.0262 (5)
H30.24790.55750.20010.031*
C40.14931 (12)0.3085 (4)0.21906 (9)0.0257 (5)
C50.09692 (13)0.2284 (5)0.26516 (10)0.0316 (5)
H50.05480.09620.25670.038*
C60.10392 (13)0.3335 (5)0.32258 (10)0.0327 (5)
H60.06790.27730.35350.039*
C70.16600 (13)0.5242 (5)0.33243 (9)0.0283 (5)
C80.25217 (13)0.8178 (5)0.37491 (10)0.0297 (5)
C90.13521 (13)0.1884 (4)0.15724 (9)0.0269 (5)
H90.1225−0.01190.16240.032*
C100.05931 (13)0.3205 (5)0.12640 (9)0.0308 (5)
H10A0.01000.29240.15150.037*
H10B0.06860.52160.12270.037*
C110.04212 (14)0.1998 (6)0.06457 (10)0.0379 (6)
H11A0.02550.00420.06860.045*
H11B−0.00460.30070.04530.045*
C120.11783 (14)0.2186 (5)0.02536 (10)0.0362 (5)
H12A0.13040.41480.01730.043*
H12B0.10580.1270−0.01340.043*
C130.19283 (15)0.0828 (5)0.05528 (10)0.0358 (5)
H13A0.24200.10710.02990.043*
H13B0.1825−0.11750.05950.043*
C140.21039 (13)0.2080 (5)0.11680 (9)0.0317 (5)
H14A0.22610.40410.11210.038*
H14B0.25790.11060.13590.038*
C150.28665 (14)0.9685 (5)0.42765 (10)0.0338 (5)
H15A0.24081.01870.45440.041*
H15B0.31311.14130.41410.041*
C160.34984 (14)0.7987 (5)0.46210 (10)0.0347 (5)
C170.42421 (19)0.7598 (7)0.55380 (13)0.0591 (8)
H17A0.40540.56870.56120.071*
H17B0.47840.75190.53370.071*
C180.4327 (2)0.9083 (9)0.61010 (14)0.0775 (11)
H18A0.45441.09370.60260.116*
H18B0.47110.80880.63690.116*
H18C0.37830.92250.62880.116*
C190.42883 (14)0.6559 (5)0.28894 (12)0.0403 (6)
H19A0.40390.52280.26100.060*
H19B0.43250.57390.32900.060*
H19C0.48460.70460.27570.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0292 (3)0.0237 (3)0.0402 (3)−0.0018 (2)0.0030 (2)0.0002 (3)
O10.0286 (8)0.0414 (9)0.0276 (8)−0.0026 (7)0.0032 (6)−0.0066 (7)
O20.0576 (12)0.0484 (11)0.0531 (11)0.0198 (10)−0.0138 (9)−0.0149 (10)
O30.0490 (10)0.0465 (11)0.0368 (9)0.0081 (9)−0.0149 (8)−0.0089 (8)
O4A0.0363 (10)0.0412 (12)0.0402 (11)−0.0020 (9)0.0010 (8)0.0072 (9)
O4B0.058 (9)0.030 (7)0.083 (9)−0.013 (6)−0.001 (8)−0.008 (7)
C10.0227 (10)0.0267 (11)0.0302 (10)0.0026 (9)−0.0007 (8)−0.0023 (9)
C20.0211 (9)0.0254 (11)0.0294 (10)0.0025 (9)0.0000 (8)−0.0003 (9)
C30.0242 (10)0.0272 (11)0.0271 (10)0.0014 (9)−0.0001 (8)−0.0002 (9)
C40.0251 (10)0.0253 (11)0.0266 (10)0.0027 (9)−0.0009 (8)−0.0011 (9)
C50.0279 (11)0.0319 (12)0.0350 (11)−0.0035 (10)−0.0028 (9)−0.0014 (10)
C60.0267 (10)0.0405 (13)0.0312 (11)−0.0049 (10)0.0050 (9)−0.0006 (11)
C70.0251 (10)0.0318 (12)0.0279 (10)0.0028 (9)−0.0016 (8)−0.0043 (10)
C80.0245 (10)0.0308 (12)0.0336 (11)−0.0002 (9)0.0002 (9)−0.0048 (10)
C90.0313 (11)0.0222 (11)0.0270 (10)−0.0006 (9)−0.0023 (8)−0.0014 (9)
C100.0248 (10)0.0342 (12)0.0335 (11)−0.0021 (10)−0.0017 (9)−0.0003 (10)
C110.0323 (12)0.0469 (15)0.0341 (12)−0.0067 (11)−0.0080 (9)0.0010 (11)
C120.0384 (12)0.0431 (14)0.0270 (11)−0.0051 (11)−0.0041 (9)−0.0024 (11)
C130.0416 (13)0.0358 (13)0.0301 (11)0.0010 (11)0.0030 (10)−0.0049 (11)
C140.0297 (11)0.0350 (12)0.0305 (11)0.0053 (10)−0.0016 (9)−0.0043 (10)
C150.0338 (11)0.0365 (13)0.0309 (11)0.0016 (10)−0.0017 (9)−0.0073 (10)
C160.0322 (12)0.0371 (13)0.0346 (12)−0.0027 (11)−0.0018 (9)−0.0044 (11)
C170.0637 (18)0.0570 (18)0.0557 (17)0.0124 (16)−0.0278 (15)−0.0027 (15)
C180.077 (2)0.102 (3)0.0525 (18)0.025 (2)−0.0274 (16)−0.0068 (19)
C190.0274 (11)0.0317 (13)0.0620 (16)0.0040 (10)0.0077 (11)0.0001 (12)
Geometric parameters (Å, °) top
S1—O4B1.463 (2)C10—H10A0.9900
S1—O4A1.4641 (19)C10—H10B0.9900
S1—C11.765 (2)C11—C121.517 (3)
S1—C191.780 (2)C11—H11A0.9900
O1—C81.375 (3)C11—H11B0.9900
O1—C71.380 (2)C12—C131.520 (3)
O2—C161.193 (3)C12—H12A0.9900
O3—C161.325 (3)C12—H12B0.9900
O3—C171.460 (3)C13—C141.526 (3)
C1—C81.338 (3)C13—H13A0.9900
C1—C21.439 (3)C13—H13B0.9900
C2—C71.387 (3)C14—H14A0.9900
C2—C31.392 (3)C14—H14B0.9900
C3—C41.391 (3)C15—C161.510 (3)
C3—H30.9500C15—H15A0.9900
C4—C51.399 (3)C15—H15B0.9900
C4—C91.514 (3)C17—C181.455 (4)
C5—C61.385 (3)C17—H17A0.9900
C5—H50.9500C17—H17B0.9900
C6—C71.377 (3)C18—H18A0.9800
C6—H60.9500C18—H18B0.9800
C8—C151.487 (3)C18—H18C0.9800
C9—C141.527 (3)C19—H19A0.9800
C9—C101.533 (3)C19—H19B0.9800
C9—H91.0000C19—H19C0.9800
C10—C111.523 (3)
O4B—S1—O4A119.5 (6)C10—C11—H11B109.3
O4B—S1—C1107.5 (6)H11A—C11—H11B108.0
O4A—S1—C1111.19 (10)C11—C12—C13111.10 (19)
O4B—S1—C19114.0 (6)C11—C12—H12A109.4
O4A—S1—C19105.79 (12)C13—C12—H12A109.4
C1—S1—C1996.58 (11)C11—C12—H12B109.4
C8—O1—C7105.52 (16)C13—C12—H12B109.4
C16—O3—C17116.1 (2)H12A—C12—H12B108.0
C8—C1—C2107.52 (19)C12—C13—C14110.96 (19)
C8—C1—S1122.73 (17)C12—C13—H13A109.4
C2—C1—S1129.54 (16)C14—C13—H13A109.4
C7—C2—C3119.77 (19)C12—C13—H13B109.4
C7—C2—C1104.63 (18)C14—C13—H13B109.4
C3—C2—C1135.6 (2)H13A—C13—H13B108.0
C4—C3—C2118.8 (2)C13—C14—C9111.91 (18)
C4—C3—H3120.6C13—C14—H14A109.2
C2—C3—H3120.6C9—C14—H14A109.2
C3—C4—C5119.3 (2)C13—C14—H14B109.2
C3—C4—C9121.74 (19)C9—C14—H14B109.2
C5—C4—C9118.92 (19)H14A—C14—H14B107.9
C6—C5—C4122.8 (2)C8—C15—C16112.1 (2)
C6—C5—H5118.6C8—C15—H15A109.2
C4—C5—H5118.6C16—C15—H15A109.2
C7—C6—C5116.3 (2)C8—C15—H15B109.2
C7—C6—H6121.9C16—C15—H15B109.2
C5—C6—H6121.9H15A—C15—H15B107.9
C6—C7—O1126.1 (2)O2—C16—O3124.2 (2)
C6—C7—C2123.0 (2)O2—C16—C15125.1 (2)
O1—C7—C2110.79 (18)O3—C16—C15110.7 (2)
C1—C8—O1111.53 (18)C18—C17—O3108.3 (2)
C1—C8—C15133.0 (2)C18—C17—H17A110.0
O1—C8—C15115.31 (19)O3—C17—H17A110.0
C4—C9—C14114.16 (17)C18—C17—H17B110.0
C4—C9—C10110.85 (17)O3—C17—H17B110.0
C14—C9—C10110.00 (18)H17A—C17—H17B108.4
C4—C9—H9107.2C17—C18—H18A109.5
C14—C9—H9107.2C17—C18—H18B109.5
C10—C9—H9107.2H18A—C18—H18B109.5
C11—C10—C9112.27 (19)C17—C18—H18C109.5
C11—C10—H10A109.2H18A—C18—H18C109.5
C9—C10—H10A109.2H18B—C18—H18C109.5
C11—C10—H10B109.2S1—C19—H19A109.5
C9—C10—H10B109.2S1—C19—H19B109.5
H10A—C10—H10B107.9H19A—C19—H19B109.5
C12—C11—C10111.51 (18)S1—C19—H19C109.5
C12—C11—H11A109.3H19A—C19—H19C109.5
C10—C11—H11A109.3H19B—C19—H19C109.5
C12—C11—H11B109.3
O4B—S1—C1—C8−13.8 (7)C2—C1—C8—O10.8 (2)
O4A—S1—C1—C8−146.31 (19)S1—C1—C8—O1−174.34 (14)
C19—S1—C1—C8103.9 (2)C2—C1—C8—C15176.7 (2)
O4B—S1—C1—C2172.3 (7)S1—C1—C8—C151.6 (4)
O4A—S1—C1—C239.7 (2)C7—O1—C8—C1−0.3 (2)
C19—S1—C1—C2−70.1 (2)C7—O1—C8—C15−176.97 (19)
C8—C1—C2—C7−0.9 (2)C3—C4—C9—C1421.3 (3)
S1—C1—C2—C7173.75 (17)C5—C4—C9—C14−160.1 (2)
C8—C1—C2—C3179.9 (2)C3—C4—C9—C10−103.6 (2)
S1—C1—C2—C3−5.4 (4)C5—C4—C9—C1075.0 (2)
C7—C2—C3—C4−1.0 (3)C4—C9—C10—C11−178.72 (18)
C1—C2—C3—C4178.1 (2)C14—C9—C10—C1154.1 (2)
C2—C3—C4—C50.1 (3)C9—C10—C11—C12−54.8 (3)
C2—C3—C4—C9178.68 (19)C10—C11—C12—C1355.2 (3)
C3—C4—C5—C60.5 (3)C11—C12—C13—C14−55.9 (3)
C9—C4—C5—C6−178.2 (2)C12—C13—C14—C956.5 (3)
C4—C5—C6—C70.0 (3)C4—C9—C14—C13179.72 (18)
C5—C6—C7—O1−179.3 (2)C10—C9—C14—C13−54.9 (2)
C5—C6—C7—C2−1.0 (3)C1—C8—C15—C16−88.6 (3)
C8—O1—C7—C6178.2 (2)O1—C8—C15—C1687.2 (2)
C8—O1—C7—C2−0.3 (2)C17—O3—C16—O20.5 (4)
C3—C2—C7—C61.5 (3)C17—O3—C16—C15−179.5 (2)
C1—C2—C7—C6−177.8 (2)C8—C15—C16—O216.1 (3)
C3—C2—C7—O1−179.89 (18)C8—C15—C16—O3−163.9 (2)
C1—C2—C7—O10.8 (2)C16—O3—C17—C18178.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O4Ai0.992.603.479 (3)149
C15—H15B···O2ii0.992.563.437 (3)147
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O4Ai0.992.603.479 (3)149
C15—H15B···O2ii0.992.563.437 (3)147
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
references
References top

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.

Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195.

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3839.

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